Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin™ approach

Chinh T. Bui; Andrew M. Bray; Yen Pham; Rhonda Campbell; Francesca Ercole; Firas A. Rasoul; N. Joe Maeji

doi:10.1023/A:1009642429617

Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin™ approach

Chinh T. Bui, Andrew M. Bray, Yen Pham, Rhonda Campbell, Francesca Ercole, Firas A. Rasoul, N. Joe Maeji

Research output: Contribution to journal › Article › Research › peer-review

8 Citations (Scopus)

Abstract

The 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid (Barany) linker and its monomethoxy analog were applied to the Multipin™ method of solid phase synthesis. A comparative assessment of reductive amination and cleavage of these linkers under conditions of multiple synthesis indicated that both were applicable to a broad range of primary amines including aniline and 4-nitroaniline. Apart from the greater lability of the dimethoxy version under TFA cleavage, there was no observable advantage of one linker over the other within the described experiment.

Original language	English
Pages (from-to)	155-163
Number of pages	9
Journal	Molecular Diversity
Volume	4
Issue number	3
DOIs	https://doi.org/10.1023/A:1009642429617
Publication status	Published - 1 Jan 1998
Externally published	Yes

Keywords

Linkers
N-alkylamides
Reductive amination
Solid-phase synthesis

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10.1023/A:1009642429617

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AU - Bui, Chinh T.

AU - Bray, Andrew M.

AU - Pham, Yen

AU - Campbell, Rhonda

AU - Ercole, Francesca

AU - Rasoul, Firas A.

AU - Maeji, N. Joe

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N2 - The 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid (Barany) linker and its monomethoxy analog were applied to the Multipin™ method of solid phase synthesis. A comparative assessment of reductive amination and cleavage of these linkers under conditions of multiple synthesis indicated that both were applicable to a broad range of primary amines including aniline and 4-nitroaniline. Apart from the greater lability of the dimethoxy version under TFA cleavage, there was no observable advantage of one linker over the other within the described experiment.

AB - The 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid (Barany) linker and its monomethoxy analog were applied to the Multipin™ method of solid phase synthesis. A comparative assessment of reductive amination and cleavage of these linkers under conditions of multiple synthesis indicated that both were applicable to a broad range of primary amines including aniline and 4-nitroaniline. Apart from the greater lability of the dimethoxy version under TFA cleavage, there was no observable advantage of one linker over the other within the described experiment.

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KW - N-alkylamides

KW - Reductive amination

KW - Solid-phase synthesis

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Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin™ approach

Abstract

Keywords

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